Tobacco



TOBACCO No Drawing. Application July 26, 1954, Seriai No. 445,893

13 Claims. (til. 131-17) This invention relates to tobacco and has foran object the provision of a smoking tobacco product having improvedaroma and flavor characteristics which become apparent during smoking.

Smoking tobacco as now prepared for use in cigarettes comprisesessentially a blended mixture of various types of tobaccos which aredesired to produce a characteristic flavor and aroma when the tobacco issmoked. Present day cigarette tobaccos normally comprise blends of (1)heat-cured tobaccos, which are sometimes known as fluecured, bright leafor Virginia tobaccos, (2) air-cured tobaccos, which are sometimes knownas burley or Kentucky and Maryland tobaccos, and (3) sun-cured tobaccos,which are known as Turkish or Oriental tobaccos. The relativeproportions of these various types blended to produce a desiredcigarette tobacco mixture depend in a large measure upon thecharacteristic flavor or aroma that is desired to be achieved when thetobacco is smoked. Also, it is common practice to add varioussubstances, such as flavoring materials and humectants, in order toprovide other desired properties.

A further object of this invention is to provide a smoking tobacco whichwhen smoked will have improved or enhanced flavor and odorcharacteristics which will be pleasing to the smoker.

A further object of this invention is the provision of a smoking tobaccohaving added thereto a compound or compounds which, when the tobacco issmoked, will liberate one or more organic acids imparting a selected anddesired flavor and aroma to the smoke.

A still further object of this invention is the provision of a tobaccoproduct having added thereto a substantially non-volatile substancewhich in itself does not substantially change the flavor or aroma of thetobacco but which, when burned on the tobacco, will release to the smokecertain desired flavoror aroma-producing acids.

A still further object of this invention is the provision of a tobaccohaving added thereto an organic compound which, when the tobacco issmoked or burned, will liberate several types of flavoring acids wherebythe desired improvement in the flavor and aroma of the smoke may beachieved.

A still further object of this invention is the provision of additivesfor tobacco which may be easily and simply prepared and which may beincorporated into the tobacco at any stage during the processingthereof.

Further and additional objects will appear from the followingdescription and the appended claims.

In the copending application of Samuel OBrien Jones, Serial No. 445,891,filed July 26, 1954, it is disclosed that certain esters offlavor-producing acids, when added to tobacco, will, when smoked orburned with the tobacco, release the acid or acids which latter impart adesired characteristic odor and/or flavor to the smoke, therebycontributing to the enjoyment of the smoker.

In accordance with the broad aspects of this invention, a smokingtobacco composition is provided which contains as an additive a smallamount of an ester of a polynited States Patent 2,766,47 iatented Got.9, 1956 hydroxy compound related to the lactones of certain sugar acids,said esters being selected from the group consisting of the monoandpolyesters of the lactones of the aldonic and uronic acids. It has beenfound that these esters, when smoked or burned with the tobacco, willrelease one or more of the esterifying acids which, to provide thedesired flavor and aroma, are those having from 3 to 8 carbon atoms.These acids, when present in the smoke in suitable concentrations,impart characteristic and desirable flavor and aroma to the tobaccosmoke, thus contributing to the enjoyment of the smoker. The additivesof this invention are substantially nonvolatile under ordinary tobaccostorage conditions and will remain dispersed throughout the tobaccountil such time as it is smoked and they are sufiiciently nonvolatile sothat they Will remain in the burning area of the tobacco to permit theacid release to occur. Obviously, the additive should not volatilizemuch ahead of the burning Zone or the desired acid release may notoccur. The additives herein disclosed are relatively stable under theusual tobacco storage conditions; consequently, the principal release offlavoring acid or acids does not occur until the tobacco is smoked.

The hydroxyl compounds which are esterified to pro duce the additives ofthis invention are the lactones of the aldonic or the uronic acids.These are polyhydric compounds and one or more of the hydroxyl groupsmay be esterified with the flavor-producing acid. Suitable lactones ofthe aldonic acid series are the pentaldonic, hexaldonic or heptaldonicacid, such as arabonic, Xylonic, lyxonic, ribonic, gluconic, galactonic,mannonic, gluonic, talonic, idonic, altronic, or allonic acid. Suitablelactones of the uronic acid series are the penturonic, hexuronic orhepturonic acid, such as araburonic, xyluronic, lyxuronic, riburonic,glucuronic, galacturonic, mannuronic, guluronic, taluronic, iduronic,altruronic or alluronic acid.

The flavor-producing esterifying acids which are released by the estersupon smoking in accordance with this invention are preferably thoseflavoring acids which will volatilize and will be carried by the smoke,such acids usually being the organic carboxylic acids having 3, 4, 5, 6,7 or 8 carbon atoms, herein collectively referred to as those havingfrom 3 to 8 carbon atoms. Representative acids are the saturatedaliphatic fatty acids, such as propionic, n-butyric, isobutyric,n-valeric, isovaleric, Z-methylbutyric, n-caproic, 4-methylvaleric, 3-methylvaleric, 2,2-dimethylbutyric, Z-methylisovaleric, straight orbranched chain heptoic, or straight or branched chain caprylic acids;the unsaturated aliphatic fatty acids, such as acrylic, crotonic,vinylacetic, 4-methyl-4-hexenoic and S-methylsorbic acids; thecycloalkane or cyeloalkene aliphatic acids, such ascyclopentanecarboxylic, cyclohexanecarboxylic, cyclopentaneacetic orcyclohexaneacetic acids or the corresponding unsaturated cycloalkenes;the aromatic carboxylic acids, such as benzoic or toluic acids; andphenylacetic acid. Also the volatile derivatives of these acids, such asthe hydroxy acids or the keto acids may be the acid compounds releasedto impart the de sired odor or flavor to the smoke. It is preferred thatthe flavoring acid be an aliphatic or alicyclic saturated monocarboxylicacid of the fatty acid series having 4, 5 or 6 carbon atoms, hereincollectively referred to as those having from 4 to 6 carbon atoms.

It will be apparent that the ester additive may be selected or preparedin such a manner that any one of the foregoing acids will be releasedduring smoking. Also a single additive or mixture of additives may beselected and added to the tobacco so that a plurality of desiredflavoring acids may be simultaneously liberated if desired, thuseffecting a blend of the various types of aromas which has thecharacteristics of the several flavoring acids. Also, if desired, theseveral hydroxyl groups in the polyhydroxy lactone compound may beesterified with one or more diflerent flavoring acids or less than allof the hydroxyl groups may be esterified to produce the additive used inaccordance with this invention. The specific flavor-producing acid oracids that are combined with the hydroxy compound to form the ester willdepend upon the flavor and aroma desired in the tobacco smoke. Asindicated above, the particular flavoring acid selected for thepreparation of the ester is of consequence only in so far as theparticular flavor contributed by that particular acid is important. Anyof the flavor-producing acids may be utilized and, as previouslyindicated, they generally comprise the saturated or unsaturated organiccarboxylic acids containing from 3 to 8 carbon atoms, preferably thesaturated aliphatic monoearboxylic acids having from 4 to 6 carbonatoms.

The additives contemplated by this invention may be incorporated intothe tobacco in any desired manner. For example, solutions of theadditive in a suitable solvent, such as alcohol, ethyl ether, acetone orthe like, may be applied to the tobacco as by spraying or otherwise,whereafter the solvent is driven off as a vapor leaving the additivethoroughly incorporated with the tobacco. The additive may also beuniformly dispersed in water and applied in a like manner if desired.The incorporation of the additive may take place at any time prior tothe final packaging of the tobacco product. In the case of cigarettetobacco, it may be incorporated before or after blending of the varioustobaccos if, in fact, blended tobacco is employed, and the additives maybe applied to one or all of the blend constituents. Under certaincircumstances the additive may be incorporated into the tobacco beforeaging and curing; however, this would not ordinarily be done if theadditive has a tendency to decompose during the aging and curingprocess. in the case of cigarettes the additive in some instances mightbe applied to the paper instead of to the tobacco.

The amount of additive in the final tobacco product contemplated by thisinvention is quite small but will vary widely with the particularadditive employed and the amount of acid released upon burning or theflavor or aroma desired in the smoke. Thus an additive that releasesonly a comparatively small fraction of its total available flavoringacid on burning will be required in higher concentrations than thoseadditives which are more eflicient with respect to the amount offlavoring acid released. Also, it is well known that some of thealiphatic fatty acids having from 4 to 6' carbon atoms have adisagreeable odor per so when vapors of these acids are smelled incertain concentrations. However, in very low concentrations they providein the tobacco smoke a desirable flavor and aroma, and the amount ofadditive in the tobacco should be such as not to ex ceed the amountwhich, when the tobacco is smoked, will release desirable quantities ofthe acid. This amount in'many cases will be determined by actualexperimentation. Generally speaking, however, desirable flavor and aromaare produced if the additives are incorporated into the final tobaccoproduct in amounts between about 0.01 and 1.0 percent by weight (drybasis).

As pointed out in the copending Jones application hereinbefore referredto, a number of methods have been employed for incorporatingacid-releasing compounds into cigarette tobacco and evaluating them foracid release. Certain of such methods are suggestive of procedures thatmay be used in actual commercial practice and include the following:

METHOD 1 One gram of shredded flue-cured tobacco was spread out on awatch glass of 10 cm. diameter. One milliliter of a solution of theadditive in a suitable solvent such as ethyl ether was added uniformlyto the tobacco from a pipette. The amounts of the additives vary but ingeneral 10 milligrams of additive were applied to the one gram sample.After the other had evaporated, the tobacco was rolled into a cigarettewhich was stored at 75 F. and about 60% relative humidity.

METHOD 2 A small quantity of liquid additive in the amount of l to Smilligrams was streaked longitudinally along the paper of a cigarette bymeans of a stirring rod.

METHOD 3 The additive was dissolved in a volatile solvent, such asacetone, alcohol or ether, using 2 to 40 milligrams of additive permilliliter of solvent. One-fourth milliliter of the resulting solutionwas then distributed through a one-inch portion (which was to be burned)of a cigarette by means of a M1 milliliter hypodermic syringe. Thevolatile solvent Was then blown out of the cigarette with a stream ofcompressed air, leaving the additive dispersed in the cigarette.

.IETHOD 4 The additive was dissolved in ethyl alcohol or other suitablesolvent and sprayed onto shredded flue-cured tobacco spread out on atable. Two hundred milliliters of solution containing 1 to 29 grams ofadditive were used for each 3 kilograms of tobacco. The tobacco wasexposed to the air until substantially all of the solvent had evaporatedand then was manufactured into cigarettes in the usual manner having anaverage weight of one gram each. These were stored for a period of l to12 months at 75 F. and 60% relative humidity in order to ascertain thestability of the additive when .stored'on tobacco.

METHOD 5 The additive was dissolved in alcohol or other suitable solventand sprayed onto one of the types of leaf tobacco that is used in ablended cigarette. This leaf tobacco was allowed to dry and was cut on ashredding machine. The shredded tobacco was blended with other types ofshredded tobaccos that had not been treated with additive and the blendwas made into cigarettes.

The compound or additive under test when applied to a low flavor tobaccoor cigarette made therefrom, as indicated in one of the foregoingmethods, was evaluated by organoleptic testing. This was carried out bysmoking the cigarette and examining the smoke by sensory methods. Ineach of these tests special efforts were made to determine whether anyacid vodor was present in the smoke. This included a careful sensorystudy of both the main stream and the side stream. If the acid odor wasdetected in either the side stream or the main stream, it was concludedthat the additive released the acid during the smoking or burning of thetreated tobacco or cigarette.

In the foregoing, reference has been made to a general class of estersof polyhydroxy lactones of the aldonic and uronic acids which are usefulas additives for tobacco in accordance with this invention. Certainof'the specific compounds in this class are new and certain of them arenot available commercially. Accordingly, se eral examples will bepresented in the following disclosing methods of preparingrepresentative compounds that are useful as additives in accordance withthis invention. In each case the compounds which were prepared by thespecific procedures given in the examples to follow were tested by oneof the methods previously mentioned and each was found to releaseflavoring acid when smoked with tobacco. It will be understood that inthe following, examples are given of preparing esters which will, uponburning or smoking of the tobacco treated therewith, liberate onlyone ofthe flavor-producing acids contemplated by this invention. However, itwill be apparent to one skilled in the art how other esters releasingother particular flavoring acids may be prepared. For example, in thefollowing where there are given examples of processes of preparingesters of one or more specific flavoring acids, it will be understoodthat essentially the same or similar means known to chemists could beemployed for preparing the esters of other flavoring acids of thecharacter hereinabove specified and that all such esters arecontemplated as additives within the scope of this invention.

Gluconoltrctone tetraisovalerate To a mixture of 5.9 grams of glucono(delta) lactone (Pfizer), 80 millileters of chloroform and 14milliliters of pyridine cooled in an ice water bath were added dropwisewith stirring over a period of 45 minutes 20 grams of isovalerylchloride. The solution was allowed to stand for three hours after whichit was heated under reflux for two hours. The reaction mixture wasdiluted with 200 millileters of ether. The ethereal solution was washedsuccessively with 100 milliliters of water, 60 milliliters of cold 2 Nsulfuric acid, 60 milliliters of water, two 60- milliliter portions of 5percent sodium bicarbonate solution and 60 milliliters of ice waterAfter the ethereal solution was dried over calcium chloride, thelow-boiling solvents were removed by distillation under reducedpressure. The residue was dissolved in ether and was treated withdecolorizing charcoal (Norite). After removal of the Norite and of theether, the product weighed 13.9 grams (87 percent yield).

Gluconolactone tetracyclopentanecarboxylate To a mixture of 6.0 grams ofgluconolactone, 100 milliliters of chloroform and 13 grams of pyridinecooled in an ice bath were added dropwise with stirring over a period offifteen minutes 21.8 grams of cyclopentanecarboxyl chloride. After onehour, the reaction mixture was heated under reflux and then was allowedto stand at room temperature for sixteen hours. The mixture was dilutedwith 200 milliliters of ether. The ethereal solution was washedsuccessively with 100 milliliters of water, 100 milliliters of 2 Nsulfuric acid, 70 milliliters of water, two SO-milliliter portionss of 5percent sodium bicarbonate and 50 milliliters of water. After thesolution was dried over calcium chloride, the low-boiling solvents wereremoved by distillation under reduced pressure. The residue wascrystallized three times from a liquid hydrocarbon (Skellysolve B),yielding 9.0 grams of solid melting at 99.5l00.5 C.

Gluconolactone tetrabenzoare To a mixture of 70 milliliters ofchloroform, 17.7 grams of benzoyl chloride and 9.9 grams of pyridinecooled in a dry ice bath were added 4.5 grams of gluconolactone. Thecooling bath was removed and the mixture was stirred for three hours. Tothe mixture were added 200 milliliters of ether and 100 milliliters ofwater. The solid material was collected by filtration and was washedwith ether. The product weighed 10.2 grams and melted at 159-160 C.Crystallization from toluene did not alter the melting point.

Galactonolactone zetracyclopentanecarboxylate To a chilled mixture of100 milliliters of chloroform, 19.5 grams of pyridine and 33.1 grams ofcyclopentanecarboxyl chloride were added 8.9 grams of galactonolactone.The mixture was allowed to warm to room temperature. After 20 hours, themixture was heated under reflux for 1.2 hours. The mixture was dilutedwith 200 milliliters of ether and the ethereal solution was washedsuccessively with 100 milliliters of water, 100 milliliters of 2 Nsulfuric acid, 100 milliliters of water, two 100- milliliter portions of5 percent sodium bicarbonate and 100 milliliters of water. After theethereal solution was dried over calcium chloride the low-boilingsolvents were removed by distillation under reduced pressure.Crystallization of the residue from hexane gave 21.5 grams of solidmetling at 77-79 C. Two further recrystallizations from hexane raisedthe melting point to 79.581 C.

Glucuronolactane triisobuzyrate' To a mixture of 5.8 grams ofglucuronolactone, 7.8 grams of pyridine and milliliters of chloroformchilled in a dry ice bath were added dropwise with stirring 11.7 gramsof isobutyryl chloride. The mixture was allowed to warm slowly to roomtemperature after which it was heated under reflux for 1.5 hours. Themixture was diluted with 250 milliliters of ether and the etherealsolution was washed successively with 100 milliliters of water, 100milliliters of 2 N sulfuric acid, 100 milliliters of water, two100-milliliter portions of 5 per cent sodium bicarbonate solution and100 milliliters of water. After the ethereal solution was dried overcalcium chloride, the low-boiling solvents were removed by distillationunder reduced pressure. The residue, 9.8 grams, was partitioned between70 percent petroleum ether-30 percent ether and 70 percent methanol30percent water. The petroleum ether-ether layers yielded 4.4 grams (35percent) of the product,

Glucuronolactone triisovalerate To a mixture of 8.8 gramsglucuronolactone (Corn Products Sales Co.), 16 milliliters of pyridineand 75 milliliters of freshly distilled chloroform chilled in a dry icebath were added dropwise with stirring over a period of 30 minutes 25grams 10f isovaleryl chloride. The cooling bath was removed and themixture was allowed to stand for one hour after which it was heatedunder reflux for two hours. After twenty hours, the mixture was dilutedwith 300 milliliters of other. The ethereal solution was washedsuccessively with two l00-milliliter portions of ice water, two100-milliliter portions of 2 N sulfuric acid, 50 milliliters of water,two 100-milliliter portions of 5 percent sodium bicarbonate solution and100 milliliters of water, After the ethereal solution was dried overcalcium chloride, the ether was removed under reduced pressure. Theresidue weighed 19.5 grams.

Glucuronolactone tricyclolzexanecarboxylate To a mixture of 5.8 grams ofglucuronolactone, 7.8 grams of pyridine and 100 milliliters ofchloroform cooled in a dry ice bath were added dropwise with stirring16.1 grams of cyclohexanecarboxyl chloride. The mixture Was allowed towarm gradually to room temperature and was heated under reflux for 2hours. The mixture was diluted with 200 milliliters of ether and waswashed successively with 100 milliliters of water, 100 milliliters of 2N sulfuric acid, 100 milliliters of water, two 100-milliliter portionsof 5 percent sodium bicarbonate solution and 100 milliliters of water.After the ethereal solution was dried over calcium chloride, thelow-boiling solvents were removed by distillation under reducedpressure. The residue, 16.2 grams, was crystallized successively fromhexane, from a mixture of hexane and isopropyl ether and fnom methanol,giving 4.3 grams of product (26 percent) melting at 121122.5 C

Glucuronolactone tribenzoate To a mixture of 8.8 grams ofglucuronolactone, 100 milliliters of chloroform and 20 grams of pyridinecooled in ice water were added, with stirring, over a period of 0.5 hour35.1 grams of benzoyl chloride. The mixture was stirred at roomtemperature for 2 hours after which it was heated under reflux for 2hours. The reaction mixture was diluted with 250 milliliters of etherand the mixture was washed with 100 milliliters of water. The insolublesolid was collected by filtration and was washed with two SO-milliliterportions of 5 percent sodium bicarbonate. The ethereal filtrate waswashed successively with 70 milliliters of 2 N sulfuric acid, 100milliliters of water, two 60-milliliter portions of 5 percent sodiumbicarbonate and 100 milliliters of water. The ethereal solution wasdecolorized by treatment with decolorizing charcoal after which thelow-boiling solvents were re- 7 moved by distillation under reducedpressure. The residue was crystallized from isopropyl alcohol, whereby4.8 grams of solid, melting at 145 152 C., were obtained. Furthercrystallization from isopropyl alcohol followed by tworecrystaliizations from methyl alcohol raised the melting point to156.5157.5 C. The precipitate which separated from the dilution of thereaction mixture with ether and water was crystallized twice to give 6.1grams of solid melting at 192. 93 C.

It will be understood that the foregoing specific examples are onlyrepresentative of the large number of esters of the polyhydric lactonesof the uronic and aldonic acids that may be used to release acid onsmoking of the tobacco treated therewith. It will also be understoodthat these compounds may be prepared by other methods that are wellknown .to the art generally. The specific examples given are believed tobe adequate to show the manner in which a large number of esters of thevarious hydroxy compounds and the several flavoring acids may be readilyprepared.

A specific example of a method for applying an additive to a cigarettetobacco is as follows:

Three kilograms of stemmed, flue-cured tobacco were spread out on atable and were sprayed with a solution of 1.5 grams of gluconolactonetetracyclopentanecarboxylate in 200 milliliters of 95% alcohol. Thetobacco was turned from time to time during this operation in order toexpose new leaves to the spray. The treated tobacco was shredded on atobacco-cutting machine and was manufactured into cigarettes that had anaverage weight of 1 gram each. The cigarettes were stored in a roommaintained at 75 Fahrenheit and 60% relative humidity. The cigaretteswere examined by a panel of smokers shortly after manufacture, and againat the end of 90 days. The majority of the smokers detectedcyclopentanecarboxylic acid in the smoke from the cigarettes.

Studies have been made in order to determine the ex tent to whichvarious compounds will actually release acid when smoked with tobacco.As pointed out in the above-mentioned copending Jones application, anarbitrary scale has been set up for comparing or evaluating the variousadditives that may be incorporated into to bacco. The additives whichliberate the largest amount of acid on an organoleptic test basis duringsmoking have been arbitrarily assigned a rating of 10. The additives atthe bottom of the scale liberating detectable but small quantities ofacid on an organoleptic test basis have been assigned a rating of 1.Using this arbitrary scale and evaluating the various additives by atest panel of a number of smokers, the following ratings were arrived atfor certain of the compounds contemplated within the scope of thisinvention: gluconolaotone isovalerate, gluconolactonecyclopentanecarboxylate and gluconolactone benzoate each have an 3rating, galactonolactone cyclopentanecarboxylate has a 9 rating, andglucuronolactone isobutyrate, glucuronolactone isovalerate,glucuronolactone cyclchexanecarboxylate and glucuronolactone benzoateeach have a 10 rating.

While the rating given a particular compound is indicative of acidrelease, it is not necessarily conclusive in evaluating that compoundfor comercial use as a tobacco additive. For example, some compoundshaving a high rating may have a tendency to be unstable under tobaccostorage conditions, thereby prematurely releasing the acid, it beingunderstood that it is generally desirable for the acid not to bereleased prior to smoking. Also it is pointed out that the polyhydroxycompounds from which the esters are prepared in accordance with thisinvention are in certain instances related to compounds naturallyoccurring in tobacco and the residue after the acid has been releaseddoes not introduce any objectionable foreign type of constituent intothe tobacco during the smoking procedure.

Also in accordance with this invention, it may in certain instanceshedesirable to employ an ester of the polyhydroxy lactone wherein iessthan all of the hydroxyl groups are esterifiedwith the flavoring acid.However, at least theoretically, such compounds are capable of releasingfewer molecules of flavoring acid per molecule of the ester. Thus, on aweight for weight basis, the polyesters may be more effective than thecorresponding monoesters. Generally, however, the degree of acid releasein each instance should be tested by actual trial since the degree ofacid :release does not always appear to be directly proportional to thenumber of esterified groups in the hydroxy compound.

It will be understood that compositions have been prepared in accordancewith this invention which have improved or enhanced aroma and flavor togive increased pleasure during smoking. Infinite variations with respectto the kinds and amounts of flavor-producing acids are possible and maybe readily controlled. The additives of this invention may beparticularly useful with tobaccos which are ordinarily low in the typeof flavor imparted by the flavoring acids. While the invention has beenspecifically described with reference to cigarettes, it will be apparentthat it has application in the manufacture of other smoking tobaccossuch as used for hand-rolled cigarettes, pipes and cigars.

While several particular embodiments of this invention are shown above,it will be understood, of course, that the invention is not to belimited thereto, since many modifications may be made, and it iscontemplated, therefore, by the appended claims, to cover any suchmodifications as fall within the true spirit and scope of thisinvention.

I claim:

1. An article of manufacture comprising tobacco and an ester of avolatile organic acid and a lactone of a sugar acid selected from thegroup consisting of the aldonic acids and the uronic acids.

2. A smoking tobacco having added thereto a small amount of an ester ofa volatile organic acid and a polyhydroxy lactone of a sugar acidselected from the group consisting of the aldonic acids and the uronicacids.

3. A smoking tobacco having added thereto a small amount of an ester ofa volatile monocarboxylic acid and a lactone of a hexose acid selectedfrom the group consisting of the aldonic acids and the uronic acids.

4. A smoking tobacco having added thereto a small amount of an ester ofa monocarboxylic acid having from 3 to 8 carbon atoms and a lactone of ahexaldonic acid.

5. A smoking tobacco having added thereto a small amount of an ester ofa monocarboxylic acid having from 3 to 8 carbon atoms and a lactone of ahexuronic acid.

6. A smoking tobacco having added thereto between about 0.01 and 1.0percent by weight (dry basis) of an ester of a volatile monocarboxylicflavoring acid having from 3 to 8 carbon atoms and a lactone of an acidselected from the group consisting of the hexaldonic acids and thehexuronic acids.

7. The tobacco recited in claim 6 wherein said lactone isgluconolactone.

8. The tobacco recited in claim 6 wherein said lactone isgalactonolactonc.

9. The tobacco recited in claim 6 wherein said lactone isglucuronolactone.

10. The tobacco recited in claim 6 wherein said acid has from 4 to 6carbon atoms.

11. An article of manufacture comprising tobacco and between about 1.0and about 0.01 percent by Weight (dry basis) of an ester of a volatileorganic acid and a lactone of a sugar acid selected from the groupconsisting of the aldonic acids and the uronic acids.

12. A smoking tobacco having added thereto between about 1.0 and about0.01 percent by weight (dry basis) of an ester of a volatile organicacid having from 3 to 8 carbon atoms and a polyhydroxy lactone of asugar acid selected from the group consisting of the aldonic acidsReferences Cited in the file of this patent and the Home aclds' M. B.Jacobs: Synthetic Food Adjuncts. Pages 13. An article of manufacturecomprising tobacco and 136442 Published by Van Nostrand Co a derivativeof a lactone of a sugar acid, said derivative 1947 upon smoking withtobacco being capable of releasing a 6 volatile organic flavoring acidselected from the group consisting of the aldonic acids and the uronicacids.

1. AN ARTICLE OF MANUFACTURE COMPRISING TOBACCO AND AN ESTER OF AVOLATILE ORGANIC ACID AND A LACTONE OF A SUGAR ACID SELECTED FROM THEGROUP CONSISTING OF THE ALDONIC ACIDS AND THE URONIC ACIDS.